WO2017028640A1 - 印刷油墨组合物及电子器件 - Google Patents
印刷油墨组合物及电子器件 Download PDFInfo
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- WO2017028640A1 WO2017028640A1 PCT/CN2016/088641 CN2016088641W WO2017028640A1 WO 2017028640 A1 WO2017028640 A1 WO 2017028640A1 CN 2016088641 W CN2016088641 W CN 2016088641W WO 2017028640 A1 WO2017028640 A1 WO 2017028640A1
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- MJTSPTRANGPNRJ-UHFFFAOYSA-N CCc1cncnc1 Chemical compound CCc1cncnc1 MJTSPTRANGPNRJ-UHFFFAOYSA-N 0.000 description 1
- SEULWJSKCVACTH-UHFFFAOYSA-N c1cnc[n]1-c1ccccc1 Chemical compound c1cnc[n]1-c1ccccc1 SEULWJSKCVACTH-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N c1cncnc1 Chemical compound c1cncnc1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N c1cnncc1 Chemical compound c1cnncc1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N c1nc(cccc2)c2[nH]1 Chemical compound c1nc(cccc2)c2[nH]1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N c1nc(cccc2)c2[o]1 Chemical compound c1nc(cccc2)c2[o]1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N c1nc(cccc2)c2[s]1 Chemical compound c1nc(cccc2)c2[s]1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 1
- KYQCOXFCLRTKLS-UHFFFAOYSA-N c1nccnc1 Chemical compound c1nccnc1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
- C09D11/033—Printing inks characterised by features other than the chemical nature of the binder characterised by the solvent
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/36—Inkjet printing inks based on non-aqueous solvents
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/52—Electrically conductive inks
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/08—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/08—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials
- C09K11/54—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials containing zinc or cadmium
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/08—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials
- C09K11/56—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials containing sulfur
- C09K11/562—Chalcogenides
- C09K11/565—Chalcogenides with zinc cadmium
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/08—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials
- C09K11/88—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials containing selenium, tellurium or unspecified chalcogen elements
- C09K11/881—Chalcogenides
- C09K11/883—Chalcogenides with zinc or cadmium
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
- H10K50/115—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising active inorganic nanostructures, e.g. luminescent quantum dots
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/10—Deposition of organic active material
- H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
- H10K71/15—Deposition of organic active material using liquid deposition, e.g. spin coating characterised by the solvent used
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/10—Deposition of organic active material
- H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
- H10K71/13—Deposition of organic active material using liquid deposition, e.g. spin coating using printing techniques, e.g. ink-jet printing or screen printing
- H10K71/135—Deposition of organic active material using liquid deposition, e.g. spin coating using printing techniques, e.g. ink-jet printing or screen printing using ink-jet printing
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Definitions
- the present invention relates to a printing ink composition
- a printing ink composition comprising an inorganic nanomaterial, the ink composition comprising at least one inorganic nanomaterial, and at least one organic solvent based on a substituted aromatic or heteroaromatic;
- An electronic device in particular an electroluminescent device, printed using this printing ink composition.
- quantum dots are nano-sized semiconductor materials with quantum confinement effects. When stimulated by light or electricity, quantum dots emit fluorescence with specific energy. The color (energy) of fluorescence is determined by the chemical composition and size of quantum dots. . Therefore, the control of the size and shape of quantum dots can effectively regulate its electrical and optical properties.
- countries are studying the application of quantum dots in full color, mainly in the display field.
- QLEDs quantum light-emitting devices
- device performance has been greatly improved, such as Peng et al., in Nature Vol5 15 96 (2015) and Qian et al., in Nature Photonics Vol9 259. (2015) reported.
- electrons and holes are injected into the light-emitting layer to illuminate under an applied electric field.
- Spin coating is currently the primary method for forming inorganic nanoparticle films.
- spin coating techniques are difficult to apply to the fabrication of large area optoelectronic devices.
- inkjet printing can Large-area and low-cost preparation of inorganic nanoparticle films; compared to traditional semiconductor production processes, inkjet printing with low energy consumption, low water consumption, and environmental protection are production technologies with great advantages and potential.
- solvent for dissolving inorganic nanoparticles particularly quantum dots
- conventionally used solvents such as toluene and chloroform tend to cause clogging of the nozzle holes due to low boiling point and easy drying, and during film formation during ejection or after ejection, The volatilization of the solvent removes the heat of vaporization, lowers the temperature of the sprayed composition, and causes precipitation of the inorganic nanomaterial.
- Viscosity and surface tension are also important parameters that affect the printing ink and printing process.
- a promising printing ink needs to have the proper viscosity and surface tension.
- quantum dot inks for printing are also reported.
- Nanoco Technologies Ltd. discloses a method of printing a printable ink formulation comprising nanoparticles (CN101878535B).
- a printable ink formulation comprising nanoparticles (CN101878535B).
- a suitable ink substrate such as toluene and dodecyl selenol
- a printable nanoparticle ink and a corresponding nanoparticle-containing film are obtained.
- the ink contains a concentration of quantum dot material, an organic solvent, and an alcohol polymer additive having a high viscosity.
- a quantum dot film was obtained by printing the ink, and a quantum dot electroluminescent device was prepared.
- QD Vision discloses a quantum dot ink formulation comprising a host material, a quantum dot material and an additive (US2010264371A1).
- a novel printing ink composition comprising an inorganic nanomaterial, the composition comprising at least one inorganic nanomaterial, and at least one substituted based aromatic A family or heteroaromatic organic solvent; the invention still further provides an electronic device, in particular a photovoltaic device, in particular an electroluminescent device, printed using the printing ink composition.
- a printing ink composition comprising at least one inorganic nanomaterial and at least one aromatic or heteroaromatic organic solvent having a substitution as shown by the general formula:
- Ar 1 is an aromatic or heteroaromatic ring having 5 to 10 carbon atoms, n ⁇ 1, R is a substituent, and the total number of atoms other than H of all substituents is greater than or equal to 2, characterized in that
- the organic solvent has a boiling point of ⁇ 180 °C. The organic solvent can be evaporated from the solvent system to form an inorganic nanomaterial film.
- the organic solvent described therein has a viscosity of @25 ° C and ranges from 1 cPs to 100 cPs.
- the organic solvent described therein has a surface tension of @25 ° C in the range of 19 dyne/cm to 50 dyne/cm.
- the organic solvent described therein has a structure represented by the following formula:
- X is CR 1 or N
- Ar 1 in the formula (I) is selected from the following structural units:
- R in the formula (I) is selected from a linear alkyl group, an alkoxy group or a thioalkoxy group having 1 to 20 C atoms, or a branch or a ring having 3 to 20 C atoms.
- the organic solvent is selected from the group consisting of: dodecylbenzene, dipentylbenzene, diethylbenzene, trimethylbenzene, tetramethylbenzene, butylbenzene, triphenylbenzene, pentyltoluene, 1-methylnaphthalene, dihexylbenzene, Dibutylbenzene, p-diisopropylbenzene, pentylbenzene, tetrahydronaphthalene, cyclohexylbenzene, chloronaphthalene, 1-tetralone, 3-phenoxytoluene, 1-methoxynaphthalene, cyclohexylbenzene , dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, benzyl benzoate, dibenzyl ether, benzyl benzoate, and the like, and any mixture thereof
- the organic solvent described therein may further comprise at least one other solvent, and the organic solvent of the formula (I) accounts for more than 50% by weight based on the total weight of the mixed solvent.
- the inorganic nanomaterial described therein is a quantum dot material, that is, the particle diameter thereof has a monodisperse size distribution, and the shape thereof may be selected from different nanotopography such as a sphere, a cube, a rod or a branched structure.
- It comprises at least one luminescent quantum dot material having an emission wavelength between 380 nm and 2500 nm.
- the at least one inorganic nanomaterial described therein is Group IV, II-VI, II-V, III-V, III-VI, IV-VI, I-III-VI of the periodic table, Group II-IV-VI, Group II-IV-V binary or multi-component semiconductor compounds or mixtures of these compounds.
- the at least one inorganic nanomaterial described therein is a luminescent quantum dot selected from the group consisting of CdSe, CdS, CdTe, ZnO, ZnSe, ZnS, ZnTe, HgS, HgSe, HgTe, CdZnSe and Any combination.
- the at least one inorganic nanomaterial described therein is a luminescent quantum dot selected from the group consisting of InAs, InP, InN, GaN, InSb, InAsP, InGaAs, GaAs, GaP, GaSb, AlP, AlN, AlAs, AlSb, CdSeTe, ZnCdSe and Any combination of them.
- the at least one inorganic nanomaterial described therein is a perovskite nanoparticle material, particularly a luminescent perovskite nanoparticle, or a metal nanoparticle material, or a metal oxide nanoparticle material, or a mixture thereof.
- the organic functional material may be selected from the group consisting of a hole injection material (HIM), a hole transport material (HTM), an electron transport material (ETM), an electron injecting material (EIM), and an electron.
- HIM hole injection material
- HTM hole transport material
- ETM electron transport material
- EIM electron injecting material
- EBM Barrier material
- HBM hole blocking material
- Emitter illuminator
- Hos host material
- the weight ratio of the inorganic nanomaterial is 0.3% to 70%, and the weight ratio of the organic solvent contained is 30% to 99.7%.
- An electronic device comprising a functional layer printed from a printing ink composition as described above, wherein the substituted aromatic or heteroaromatic based organic solvent contained in the composition is evaporated from the solvent system to Forming an inorganic nanomaterial film.
- the electronic device can be selected from a quantum dot light emitting diode (QLED), a quantum dot photovoltaic cell (QPV), a quantum dot luminescent cell (QLEEC), a quantum dot field effect transistor (QFET), a quantum dot luminescence field effect transistor, a quantum dot.
- QLED quantum dot light emitting diode
- QPV quantum dot photovoltaic cell
- QLEEC quantum dot luminescent cell
- QFET quantum dot field effect transistor
- a quantum dot luminescence field effect transistor a quantum dot.
- the present invention provides a printing ink composition comprising inorganic nanoparticles comprising at least one inorganic nanomaterial, and at least one organic solvent based on a substituted aromatic or heteroaromatic.
- the viscosity and the surface tension can be adjusted to a suitable range in accordance with a specific printing method, particularly ink jet printing, to facilitate printing, and a film having a uniform surface can be formed.
- the organic solvent based on the substituted aromatic or heteroaromatic can be effectively removed by post-treatment, such as heat treatment or vacuum treatment, which is advantageous for ensuring the performance of the electronic device.
- the present invention therefore provides a printing ink for the preparation of high quality inorganic nanoparticle films, providing a technical solution for printable electronic or optoelectronic devices.
- FIG. 1 is a structural view of a preferred light-emitting device according to the present invention, in which 101 is a substrate, 102 is an anode, 103 is a hole injection layer (HIL) or a hole transport layer (HTL), and 104 is a light-emitting layer, 105 It is an electron injection layer (EIL) or an electron transport layer (ETL), and 106 is a cathode.
- HIL hole injection layer
- HTL hole transport layer
- ETL electron transport layer
- ETL electron transport layer
- the present invention provides a composition comprising at least one inorganic nanomaterial and at least one aromatic or heteroaromatic organic solvent having a substitution represented by the following formula:
- Ar 1 is an aromatic or heteroaromatic ring having 5 to 10 carbon atoms, n ⁇ 1, R is a substituent, and the total number of atoms other than H of all substituents is greater than or equal to 2, characterized in that
- the organic solvent has a boiling point of ⁇ 180 °C. The organic solvent can be evaporated from the solvent system to form an inorganic nanomaterial film.
- the substituted aromatic or heteroaromatic solvent is represented by the formula (I) wherein Ar 1 is an aromatic or heteroaromatic ring having 5 to 10 carbon atoms.
- An aromatic group refers to a hydrocarbon group containing at least one aromatic ring, including a monocyclic group and a polycyclic ring system.
- a heteroaromatic group refers to a hydrocarbon group (containing a hetero atom) comprising at least one heteroaromatic ring, including a monocyclic group and a polycyclic ring system.
- These polycyclic rings may have two or more rings in which two carbon atoms are shared by two adjacent rings, a fused ring. At least one of these rings of the polycyclic ring is aromatic or heteroaromatic.
- examples of the aromatic group are: benzene, naphthalene, anthracene, phenanthrene, perylene, tetracene, anthracene, benzofluorene, triphenylene, anthracene, anthracene, and derivatives thereof.
- heteroaromatic groups are: furan, benzofuran, thiophene, benzothiophene, pyrrole, pyrazole, triazole, imidazole, oxazole, oxadiazole, thiazole, tetrazole, anthracene, anthracene Oxazole, pyrroloimidazole, pyrrolopyrrole, thienopyrrole, thienothiophene, furopyrrol, furanfuran, thienofuran, benzisoxazole, benzisothiazole, benzimidazole, pyridine, pyrazine, Pyridazine, pyrimidine, triazine, quinoline, isoquinoline, o-diazine, quinoxaline, phenanthridine, carbaidine, quinazoline, quinazolinone, and derivatives thereof.
- the total number of atoms other than H in all the substituents R in the general formula (I) as described above is greater than or equal to 2.
- the atoms other than H in all the substituents R described herein include atoms of C, Si, N, P, O, S, F, Cl, Br, I and the like.
- a methoxy substituent and three chlorine substituents are all included in the scope of the benzene invention, and specific examples are 1-methoxynaphthalene and trichlorobenzene.
- the total number of atoms other than H in all the substituents R in the general formula (I) as described above is large It is equal to or equal to 2, preferably 2 to 20, more preferably 2 to 10, most preferably 3 to 10.
- composition characterized by the organic solvent of the formula (I), wherein a more preferred example thereof can be further represented by the following formula:
- X is CR 1 or N
- R 1 , R 2 , R 3 are H, or D, or a linear alkyl, alkoxy or thioalkoxy group having from 1 to 10 C atoms, or A branched or cyclic alkyl, alkoxy or thioalkoxy group of 3 to 10 C atoms is either a silyl group or a substituted keto group having 1 to 10 C atoms.
- Ar 1 in formula (I) is preferably selected from the group consisting of:
- one or more of the groups R in the above formula (I) may form a monocyclic or polycyclic aliphatic or aromatic group with each other and/or a ring bonded to the group. Ring system.
- solvents are, but not limited to, 1-tetralone, 2-tetralone, 1-methoxynaphthalene, 2-methoxynaphthalene, tetrahydronaphthalene, 1-chloronaphthalene, 2-chloro Naphthalene, 1,4-dimethylnaphthalene, 1-methylnaphthalene, 2-methylnaphthalene, and the like.
- the substituted aromatic or heteroaromatic solvent-based system can effectively disperse inorganic nanoparticles, that is, as a new dispersing solvent to replace the solvent of the conventionally used dispersed inorganic nanoparticles, such as toluene, xylene, chloroform, chlorine. Benzene, dichlorobenzene, n-heptane, etc.
- the substituted aromatic or heteroaromatic organic solvent used to disperse the inorganic nanoparticles is selected to take into account its boiling point parameters.
- the substituted aromatic or heteroaromatic organic solvent has a boiling point of > 180 ° C; in certain embodiments, the substituted aromatic or heteroaromatic based The organic solvent has a boiling point ⁇ 200 ° C; in certain embodiments, the substituted aromatic or heteroaromatic organic solvent has a boiling point ⁇ 250 ° C; in other preferred embodiments, the substitution based The aromatic or heteroaromatic organic solvent has a boiling point of ⁇ 275 ° C or ⁇ 300 ° C. Boiling points in these ranges prevent jetting of inkjet print heads Mouth blockage is beneficial.
- the substituted aromatic or heteroaromatic based organic solvent can be evaporated from a solvent system to form a film comprising an inorganic nanomaterial.
- a composition comprising an organic solvent having a surface tension of @25 ° C in the range of 19 dyne/cm to 50 dyne/cm.
- the substituted aromatic or heteroaromatic organic solvent used to disperse the inorganic nanoparticles is selected to take into account its surface tension parameters. Suitable ink surface tension parameters are suitable for a particular substrate and a particular printing method.
- the surface tension of the substituted aromatic or heteroaromatic organic solvent at 25 ° C is in the range of about 19 dyne / cm to 50 dyne / cm;
- the substituted aromatic or heteroaromatic organic solvent has a surface tension at 25 ° C in the range of from about 22 dyne/cm to 35 dyne/cm; in a most preferred embodiment,
- the surface temperature of the substituted aromatic or heteroaromatic organic solvent at 25 ° C is in the range of about 25 dyne/cm to 33 dyne/cm.
- the ink according to the invention has a surface tension at 25 ° C in the range of from about 19 dyne/cm to 50 dyne/cm; more preferably in the range of from 22 dyne/cm to 35 dyne/cm; preferably in 25 dyne/ Cm to the 33dyne/cm range.
- a composition comprising an organic solvent having a viscosity of @25 ° C, in the range of from 1 cPs to 100 cPs.
- the substituted aromatic or heteroaromatic organic solvent used to disperse the inorganic nanoparticles is selected to take into account the viscosity parameters of the ink.
- the viscosity can be adjusted by different methods, such as by selection of a suitable organic solvent and concentration of the nanomaterial in the ink.
- a solvent system comprising a substituted aromatic or heteroaromatic based organic solvent according to the present invention may It is convenient for people to adjust the printing ink in an appropriate range according to the printing method used.
- the printing ink according to the present invention comprises a weight ratio of inorganic nanomaterials in the range of 0.3% to 70% by weight, preferably 0.5% to 50% by weight, more preferably 0.5% to 30% by weight, most preferably It is in the range of 1% to 10% by weight.
- the ink based on the substituted aromatic or heteroaromatic organic solvent has a viscosity at the above composition ratio of less than 100 cps; in a more preferred embodiment, the based The ink of the substituted aromatic or heteroaromatic organic solvent has a viscosity at the above composition ratio of less than 50 cps; in a most preferred embodiment, the ink based on the substituted aromatic or heteroaromatic organic solvent The viscosity at the above composition ratio is from 1.5 to 20 cps.
- the printing ink thus formulated will be particularly suitable for ink jet printing.
- An ink obtained based on a substituted aromatic or heteroaromatic solvent system that satisfies the above boiling point and surface tension parameters and viscosity parameters can form an inorganic nanoparticle film having uniform thickness and composition properties.
- Examples of, but not limited to, substituted aromatic or heteroaromatic solvents in accordance with the invention are, but are not limited to, 1-tetralone, 3-phenoxytoluene, acetophenone, 1-methoxy Naphthalene, p-diisopropylbenzene, pentylbenzene, tetrahydronaphthalene, cyclohexylbenzene, chloronaphthalene, 1,4-dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, dipentane Benzene, o-diethylbenzene, m-diethylbenzene, p-diethylbenzene, 1,2,3,4-tetramethylbenzene, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, Butylbenzene, dodecylbenzene, 1-methylnaphthalene,
- the solvent is selected from the group consisting of: dodecylbenzene, dipentylbenzene, diethylbenzene, trimethylbenzene, tetramethylbenzene, trimenylbenzene, pentyltoluene, 1-methylnaphthalene, dihexylbenzene, dibutylbenzene, and diiso-benzene.
- the present invention relates to a printing ink composition
- a printing ink composition comprising a single substituted aromatic or heteroaromatic based organic solvent.
- the present invention relates to a printing ink composition
- a printing ink composition comprising a mixture of two or more organic solvents based on substituted aromatic or heteroaromatic.
- the substituted ink-based aromatic or heteroaromatic organic solvent system employed in the printing ink composition of the present invention may further comprise at least one other solvent, and the formula (I)
- the organic solvent accounts for more than 50% of the total weight of the mixed solvent.
- the organic solvent of formula (I) is included in an amount of at least 70% by weight based on the total weight of the solvent; more preferably, the organic solvent of formula (I) is included in an amount of at least 90% by weight based on the total weight of the solvent.
- the substituted aromatic or heteroaromatic based solvent system comprises at least 99% by weight of an organic solvent of the formula (I) or consists essentially of an organic solvent of the formula (I), or It consists entirely of the organic solvent of the formula (I).
- the substituted aromatic or heteroaromatic based organic solvent system employed in the printing ink compositions of the present invention is dodecylbenzene.
- the substituted aromatic or heteroaromatic organic solvent system employed in the printing ink compositions of the present invention is a mixture of dodecylbenzene and at least one other solvent, and ten Dialkylbenzene accounts for at least 50% of the total weight of the mixed solvent; More preferably, the dodecylbenzene comprises at least 70% by weight based on the total weight of the mixed solvent; more preferably, the dodecylbenzene comprises at least 90% by weight based on the total weight of the mixed solvent.
- the substituted aromatic or heteroaromatic based organic solvent system employed in the printing ink compositions of the present invention is 1-tetralone.
- the substituted aromatic or heteroaromatic organic solvent system employed in the printing ink compositions of the present invention is a mixture of 1-tetralone and at least one other solvent, and 1-tetralone is at least 50% by weight based on the total weight of the mixed solvent; more preferably, 1-tetralone is at least 70% by weight based on the total weight of the mixed solvent; more preferably, 1-tetralone is a mixed solvent. At least 90% of the total weight.
- the substituted aromatic or heteroaromatic based organic solvent system employed in the printing ink compositions of the present invention is 3-phenoxytoluene.
- the substituted aromatic or heteroaromatic organic solvent system employed in the printing ink composition of the present invention is a mixture of 3-phenoxytoluene and at least one other solvent, and 3-phenoxytoluene is at least 50% by weight based on the total weight of the mixed solvent; more preferably, 3-phenoxytoluene is at least 70% by weight based on the total weight of the mixed solvent; more preferably, 3-phenoxytoluene is a mixed solvent. At least 90% of the total weight.
- the substituted aromatic or heteroaromatic based organic solvent system employed in the printing ink compositions of the present invention is 3-isopropylbiphenyl.
- the substituted aromatic or heteroaromatic organic solvent system employed in the printing ink compositions of the present invention is a mixture of 3-isopropylbiphenyl and at least one other solvent, And 3-isopropylbiphenyl is at least 50% by weight based on the total weight of the mixed solvent; more preferably, 3-isopropylbiphenyl is at least 70% by weight based on the total weight of the mixed solvent; Preferably, 3-isopropylbiphenyl is at least 90% by weight based on the total weight of the mixed solvent.
- the substituted aromatic or heteroaromatic based organic solvent system employed in the printing ink compositions of the present invention is cyclohexylbenzene.
- the substituted aromatic or heteroaromatic organic solvent system employed in the printing ink composition of the present invention is a mixture of cyclohexylbenzene and at least one other solvent, and cyclohexylbenzene More preferably, the cyclohexylbenzene comprises at least 70% by weight based on the total weight of the mixed solvent; more preferably, the cyclohexylbenzene comprises at least 90% by weight based on the total weight of the mixed solvent.
- the substituted aromatic or heteroaromatic organic solvent system employed in the printing ink compositions of the present invention is 1-methoxynaphthalene.
- the substituted aromatic or heteroaromatic organic solvent system employed in the printing ink compositions of the present invention is a mixture of 1-methoxynaphthalene and at least one other solvent, and 1-methoxynaphthalene accounts for at least 50% by weight of the total mixed solvent; more preferably, 1-methoxynaphthalene accounts for at least 70% by weight based on the total weight of the mixed solvent; more preferably, 1-methoxynaphthalene accounts for a mixed solvent. At least 90% of the total weight.
- the substituted aromatic or heteroaromatic organic solvent system employed in the printing ink compositions of the present invention is 1,4-dimethylnaphthalene.
- the substituted aromatic or heteroaromatic organic solvent system employed in the printing ink compositions of the present invention is a mixture of 1,4-dimethylnaphthalene and at least one other solvent.
- 1,4-dimethylnaphthalene accounts for at least 50% by weight of the total mixed solvent; more preferably, 1,4-dimethylnaphthalene accounts for at least 70% by weight based on the total weight of the mixed solvent; more preferably, 1,4 - dimethylnaphthalene accounts for at least 90% of the total weight of the mixed solvent.
- the substituted aromatic or heteroaromatic organic solvent system employed in the printing ink compositions of the present invention is p-methyl cumene.
- the substituted aromatic or heteroaromatic organic solvent system employed in the printing ink compositions of the present invention is a mixture of p-methyl cumene and at least one other solvent, and
- the p-methyl cumene is at least 50% by weight based on the total weight of the mixed solvent; more preferably, the p-methyl cumene is at least 70% by weight based on the total weight of the mixed solvent; more preferably, the p-methyl cumene is a mixed solvent. At least 90% of the total weight.
- the substituted aromatic or heteroaromatic organic solvent system employed in the printing ink compositions of the present invention is diethylbenzene.
- the substituted aromatic or heteroaromatic organic solvent system employed in the printing ink composition of the present invention is a mixture of diethylbenzene and at least one other solvent, and diethylbenzene. At least 50% by weight based on the total weight of the mixed solvent; more preferably, p-diethylbenzene is at least 70% by weight based on the total weight of the mixed solvent; more preferably, diethylbenzene is at least 90% by weight based on the total weight of the mixed solvent.
- the substituted aromatic or heteroaromatic based organic solvent system employed in the printing ink compositions of the present invention is dibenzyl ether.
- the substituted aromatic or heteroaromatic organic solvent system employed in the printing ink compositions of the present invention is a mixture of dibenzyl ether and at least one other solvent, and bisbenzyl ether At least 50% by weight based on the total weight of the mixed solvent; more preferably, the p-benzyl ether is at least 70% by weight based on the total weight of the mixed solvent; more preferably, the dibenzyl ether is at least 90% by weight based on the total weight of the mixed solvent.
- the printing ink further comprises another organic solvent Agent.
- organic solvents include, but are not limited to, methanol, ethanol, 2-methoxyethanol, dichloromethane, chloroform, chlorobenzene, o-dichlorobenzene, tetrahydrofuran, anisole, morpholine, toluene, O-xylene, m-xylene, p-xylene, 1,4 dioxane, acetone, methyl ethyl ketone, 1,2 dichloroethane, 3-phenoxytoluene, 1,1,1 -trichloroethane, 1,1,2,2-tetrachloroethane, ethyl acetate, butyl acetate, dimethylformamide, dimethylacetamide, dimethyl sulfoxide, tetrahydronaphthalene, naphthalene Alkanes, hydrazines and/or mixtures thereof.
- the printing ink may further comprise one or more components such as surface active compounds, lubricants, wetting agents, dispersing agents, hydrophobic agents, adhesives, etc., for adjusting viscosity, film forming properties, and improving adhesion. Wait.
- the printing ink can be deposited by various techniques to obtain a quantum dot film, and suitable printing or coating techniques include, but are not limited to, inkjet printing, Nozzle Printing, typography, screen printing, dip coating, Spin coating, blade coating, roller printing, reverse roll printing, lithographic printing, flexographic printing, rotary printing, spray coating, brushing or pad printing, slit-type extrusion coating, and the like.
- Preferred printing techniques are gravure, inkjet and inkjet printing.
- printing inks suitable for inkjet printing require adjustment of the surface tension, viscosity, and wettability of the ink so that the ink can be ejected through the nozzle at a printing temperature (such as room temperature, 25 ° C) without being sprayed. Drying on the nozzle or clogging the nozzle, or forming a continuous, flat and defect-free film on a particular substrate.
- the printing ink according to the invention comprises at least one inorganic nanomaterial.
- the printing ink is characterized in that the at least one inorganic nanomaterial is preferably an inorganic semiconductor nanoparticle material.
- the inorganic nanomaterials have an average particle size in the range of from about 1 to 1000 nm. In certain preferred embodiments, the inorganic nanomaterials have an average particle size of from about 1 to 100 nm. In some more preferred embodiments, the inorganic nanomaterials have an average particle size of from about 1 to 20 nm, preferably from 1 to 10 nm.
- the inorganic nanomaterials may be selected from different shapes including, but not limited to, different nanotopography such as spheres, cubes, rods, discs or branched structures, as well as mixtures of particles of various shapes.
- the inorganic nanomaterial is a quantum dot material having a very narrow, monodisperse size distribution, i.e., the size difference between the particles and the particles is very small.
- the deviation of the monodisperse quantum dots in the size of the root mean square is less than 15% rms; more preferably, the deviation of the monodisperse quantum dots in the size of the root mean square is less than 10% rms; optimally, monodisperse Quantum dots have a root mean square deviation of less than 5% rms in size.
- the inorganic nanomaterial is a luminescent material.
- the luminescent inorganic nanomaterial is a quantum dot luminescent material.
- luminescent quantum dots can illuminate at wavelengths between 380 nanometers and 2500 nanometers.
- the luminescent wavelength of a quantum dot having a CdS core is in the range of about 400 nm to 560 nm; the luminescent wavelength of a quantum dot having a CdSe nucleus is in the range of about 490 nm to 620 nm; the luminescent wavelength of a quantum dot having a CdTe core Located at about 620 nanometers to The 680 nm range;
- the quantum wavelength of the quantum dots having the InGaP core is in the range of about 600 nm to 700 nm;
- the wavelength of the quantum dots having the PbS core is in the range of about 800 nm to 2500 nm; and the wavelength of the quantum dots having the PbSe core is located
- the wavelength of the quantum dots having the CuInGaS core is in the range of about 600 nm to 680 nm; the wavelength of the wavelength of
- the quantum dot material comprises at least one blue light having a peak wavelength of 450 nm to 460 nm, or green light having a peak wavelength of 520 nm to 540 nm, or a peak wavelength of 615 nm to 630 nm. Red light, or a mixture of them.
- the quantum dots contained may be selected from a particular chemical composition, topographical structure, and/or size to achieve light that emits the desired wavelength under electrical stimulation.
- a particular chemical composition, topographical structure, and/or size to achieve light that emits the desired wavelength under electrical stimulation.
- quantum dots For the relationship between the luminescent properties of quantum dots and their chemical composition, morphology and/or size, see Annual Review of Material Sci., 2000, 30, 545-610; Optical Materials Express., 2012, 2, 594-628; Nano Res, 2009. , 2, 425-447. The entire contents of the above-listed patent documents are hereby incorporated by reference.
- the narrow particle size distribution of the quantum dots enables quantum dots to have a narrower luminescence spectrum (J. Am. Chem. Soc., 1993, 115, 8706; US 20150108405). Furthermore, depending on the chemical composition and structure employed, the size of the quantum dots needs to be adjusted accordingly within the above-described size range to achieve the luminescent properties of the desired wavelength.
- the luminescent quantum dots are semiconductor nanocrystals.
- semi-conducting The size of the bulk nanocrystals ranges from about 5 nanometers to about 15 nanometers. Furthermore, depending on the chemical composition and structure employed, the size of the quantum dots needs to be adjusted accordingly within the above-described size range to achieve the luminescent properties of the desired wavelength.
- the semiconductor nanocrystal includes at least one semiconductor material, wherein the semiconductor material may be selected from Group IV, II-VI, II-V, III-V, III-VI, IV-VI of the periodic table, Group I-III-VI, Group II-IV-VI, Group II-IV-V binary or multi-component semiconductor compounds or mixtures thereof.
- Examples of specific semiconductor materials include, but are not limited to, Group IV semiconductor compounds composed of elemental Si, Ge, C, and binary compounds SiC, SiGe; Group II-VI semiconductor compounds, including binary compounds including CdSe, CdTe, CdO, CdS, CdSe, ZnS, ZnSe, ZnTe, ZnO, HgO, HgS, HgSe, HgTe, ternary compounds including CdSeS, CdSeTe, CdSTe, CdZnS, CdZnSe, CdZnTe, CgHgS, CdHgSe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, HgZnS, HgSeSe and quaternary compounds include CgHgSeS, CdHgSeTe, CgHgSTe, CdZnSeS, CdZn
- the luminescent quantum dots comprise a Group II-VI semiconductor material, preferably selected from the group consisting of CdSe, CdS, CdTe, ZnO, ZnSe, ZnS, ZnTe, HgS, HgSe, HgTe, CdZnSe, and any combination thereof.
- this material is used as a luminescent quantum dot for visible light due to the relatively mature synthesis of CdSe.
- the luminescent quantum dots comprise a Group III-V semiconductor material, preferably selected from the group consisting of InAs, InP, InN, GaN, InSb, InAsP, InGaAs, GaAs, GaP, GaSb, AlP, AlN, AlAs, AlSb, CdSeTe, ZnCdSe and any combination thereof.
- the luminescent quantum dots comprise a Group IV-VI semiconductor material, preferably selected from the group consisting of PbSe, PbTe, PbS, PbSnTe, Tl 2 SnTe 5, and any combination thereof.
- the quantum dots are a core-shell structure.
- the core and the shell respectively comprise one or more semiconductor materials, either identically or differently.
- the core of the quantum dot may be selected from the group IV, II-VI, II-V, III-V, III-VI, IV-VI, I-III-VI of the periodic table, Group II-IV-VI, Group II-IV-V binary or multi-element semiconductor compounds.
- quantum dot nuclei include, but are not limited to, ZnO, ZnS, ZnSe, ZnTe, CdO, CdS, CdSe, CdTe, MgS, MgSe, GaAs, GaN, GaP, GaSe, GaSb, HgO, HgS, HgSe, An alloy or mixture of HgTe, InAs, InN, InSb, AlAs, AlN, AlP, AlSb, PbO, PbS, PbSe, PbTe, Ge, Si, and any combination thereof.
- the shell of the quantum dot is selected from the same or different semiconductor materials of the core.
- Semiconductor materials that can be used for the shell include Group IV, II-VI, II-V, III-V, III-VI of the Periodic Table of the Elements. Group, Group IV-VI, Group I-III-VI, Group II-IV-VI, Group II-IV-V binary or multi-component semiconductor compounds.
- quantum dot nuclei include, but are not limited to, ZnO, ZnS, ZnSe, ZnTe, CdO, CdS, CdSe, CdTe, MgS, MgSe, GaAs, GaN, GaP, GaSe, GaSb, HgO, HgS, HgSe, An alloy or mixture of HgTe, InAs, InN, InSb, AlAs, AlN, AlP, AlSb, PbO, PbS, PbSe, PbTe, Ge, Si, and any combination thereof.
- the quantum dots having a core-shell structure may include a single layer or a multilayer structure.
- the shell includes one or more semiconductor materials that are the same or different from the core.
- the shell has a thickness of from about 1 to 20 layers.
- the shell has a thickness of about 5 to 10 layers.
- two or more shells are included on the surface of the quantum dot core.
- the semiconductor material used for the shell has a larger band gap than the core.
- the core nucleus has a type I semiconductor heterojunction structure.
- the semiconductor material used for the shell has a smaller band gap than the core.
- the semiconductor material used for the shell has an atomic crystal structure that is the same as or close to the core. Such a choice is beneficial to reduce the stress between the core shells and make the quantum dots more stable.
- the core-shell quantum dots employed are (but are not limited to):
- Red light CdSe/CdS, CdSe/CdS/ZnS, CdSe/CdZnS, etc.
- Green light CdZnSe/CdZnS, CdSe/ZnS, etc.
- Blue light CdS/CdZnS, CdZnS/ZnS, etc.
- a preferred method of preparing quantum dots is a colloidal growth method.
- the method of preparing monodisperse quantum dots is selected from the group consisting of hot-inject and/or heating-up.
- the preparation method is contained in the document Nano Res, 2009, 2, 425-447; Chem. Mater., 2015, 27(7), pp 2246-2285. The entire contents of the above-listed documents are hereby incorporated by reference.
- the surface of the quantum dot comprises an organic ligand.
- Organic ligands can control the growth process of quantum dots, regulate the appearance of quantum dots and reduce surface defects of quantum dots to improve the luminous efficiency and stability of quantum dots.
- the organic ligand may be selected from the group consisting of pyridine, pyrimidine, furan, amine, alkylphosphine, alkylphosphine oxide, alkylphosphonic acid or alkylphosphinic acid, alkyl mercaptan and the like.
- organic ligands include, but are not limited to, tri-n-octylphosphine, tri-n-octylphosphine oxide, trihydroxypropylphosphine, tributylphosphine, tris(dodecyl)phosphine, dibutyl phosphite , tributyl phosphite, octadecyl phosphite, trilauryl phosphite, tris(dodecyl) phosphite, triisodecyl phosphite, bis(2-ethylhexyl) phosphate, Tris(tridecyl)phosphate, hexadecylamine, oleylamine, octadecylamine, bisoctadecylamine, octadecylamine, bis(2-ethylhexyl)amine, oleyl
- the surface of the quantum dot comprises an inorganic ligand.
- Quantum dots protected by inorganic ligands can be obtained by ligand exchange of organic ligands on the surface of quantum dots. Examples of specific inorganic ligands include, but are not limited to, S 2- , HS - , Se 2- , HSe - , Te 2- , HTe - , TeS 3 2- , OH - , NH 2 - , PO 4 3- , MoO 4 2- , and so on. Examples of such inorganic ligand quantum dots can be found in documents: J. Am. Chem. Soc. 2011, 133, 10612-10620; ACS Nano, 2014, 9, 9388-9402. The entire contents of the above-listed documents are hereby incorporated by reference.
- the quantum dot surface has one or more of the same or different ligands.
- the luminescence spectrum exhibited by the monodisperse quantum dots has a symmetrical peak shape and a narrow half width.
- the better the monodispersity of quantum dots the more symmetric the luminescence peaks are and the narrower the half-width.
- the quantum dots have a full width at half maximum of less than 70 nanometers; more preferably, the quantum dots have a full width at half maximum of less than 40 nanometers; most preferably, the quantum dots have a full width at half maximum of less than 30 nanometers.
- the quantum dots have a luminescence quantum efficiency of 10% to 100%.
- the quantum dots have a luminescence quantum efficiency greater than 50%; more preferably, the quantum dots have a luminescence quantum efficiency greater than 80%; most preferably, the quantum dots have a luminescence quantum efficiency greater than 90%.
- the luminescent semiconductor nanocrystals are nanorods.
- the properties of nanorods are different from those of spherical nanocrystals.
- the luminescence of the nanorods is polarized along the long rod axis, while the luminescence of the spherical grains is unpolarized (see Woggon et al, Nano Lett., 2003, 3, p509).
- Nanorods have excellent optical gain characteristics, making them possible to use as laser gain materials (see Banin et al. Adv. Mater. 2002, 14, p317).
- the luminescence of the nanorods can be reversibly turned on and off under the control of an external electric field (see Banin et al, Nano Lett.
- nanorods can be preferentially incorporated into the device of the present invention under certain circumstances.
- preparation of the semiconductor nanorods are, for example, WO03097904A1, US2008188063A1, US2009053522A1, and KR20050121443A, the entire contents of each of which are hereby incorporated by reference.
- the inorganic nanomaterial is a perovskite nanoparticle material, and particularly preferred is a luminescent perovskite nanoparticle material.
- the perovskite nanoparticle material has a structural formula of AMX 3 wherein A may be selected from an organic amine or an alkali metal cation, M may be selected from a metal cation, and X may be selected from an oxygen or a halogen anion.
- CsPbCl 3 CsPb(Cl/Br) 3 , CsPbBr 3 , CsPb(I/Br) 3 , CsPbI 3 , CH 3 NH 3 PbCl 3 , CH 3 NH 3 Pb (Cl/Br 3 , CH 3 NH 3 PbBr 3 , CH 3 NH 3 Pb(I/Br) 3 , CH 3 NH 3 PbI 3 and the like.
- perovskite nanoparticle materials can be found in NanoLett., 2015, 15, 3692-3696; ACS Nano, 2015, 9, 4533-4542; Angewandte Chemie, 2015, 127(19): 5785-5788; Nano Lett., 2015, 15(4), pp 2640–2644; Adv. Optical Mater. 2014, 2, 670–678; The Journal of Physical Chemistry Letters, 2015, 6(3): 446-450; J. Mater. Chem. A, 2015 , 3, 9187-9193; Inorg. Chem. 2015, 54, 740–745; RSC Adv., 2014, 4, 55908-55911; J. Am. Chem.
- the inorganic nanomaterial is a metal nanoparticle material.
- Particularly preferred are luminescent metal nanoparticle materials.
- the metal nanoparticles include, but are not limited to, chromium (Cr), molybdenum (Mo), tungsten (W), ruthenium (Ru), rhenium (Rh), nickel (Ni), silver (Ag), copper (Cu Nanoparticles of zinc (Zn), palladium (Pd), gold (Au), hungry (Os), ruthenium (Re), iridium (Ir), and platinum (Pt).
- Cr chromium
- Mo molybdenum
- Mo tungsten
- Ru ruthenium
- Rh nickel
- silver Ag
- copper Copper
- palladium (Pd) palladium
- Au gold
- Au gold
- Ir iridium
- platinum platinum
- the inorganic nanomaterial has charge transport properties.
- the inorganic nanomaterial has electron transport capabilities.
- such inorganic nanomaterials are selected from the group consisting of n-type semiconductor materials.
- n-type inorganic semiconductor materials include, but are not limited to, metal chalcogenides, metal phosphorus group elements, or elemental semiconductors such as metal oxides, metal sulfides, metal selenides, metal deuteration , metal nitride, metal phosphide, or metal arsenide.
- the preferred n-type inorganic semiconductor material is selected from the group consisting of ZnO, ZnS, ZnSe, TiO2, ZnTe, GaN, GaP, AlN, CdSe, CdS, CdTe, CdZnSe, and any combination thereof.
- the inorganic nanomaterial has a hole transporting ability.
- such inorganic nanomaterials are selected from p-type semiconductor materials.
- the inorganic p-type semiconductor material can be selected from the group consisting of NiOx, WOx, MoOx, RuOx, VOx, CuOx, and any combination thereof.
- the printing ink according to the present invention comprises at least two and two or more inorganic nanomaterials.
- the printing ink according to the present invention further comprises at least one organic functional material.
- OLEDs hole injection materials
- HTM hole transport materials
- ETM electron transport materials
- EIM electron injecting materials
- EBM hole blocking material
- Emitter emitter
- Host host material
- the present invention also relates to a method of preparing a film comprising nanoparticles by a method of printing or coating.
- the nanoparticle-containing film is prepared by a method of inkjet printing.
- Inkjet printing for printing inks containing quantum dots of the present invention
- the machine is a commercial printer and includes drop-on-demand printheads. These printers are available from Fujifilm Dimatix (Lebanon, NH), Trident International (Brookfield, Conn.), Epson (Torrance, Calif), Hitachi Data systems Corporation (Santa Clara, Calif), Xaar PLC (Cambridge, United Kingdom), and Idanit. Technologies, Limited (Rishon Le Zion, Isreal) purchased.
- the present invention can be printed using Dimatix Materials Printer DMP-3000 (Fujifilm).
- the invention further relates to an electronic device comprising one or more functional films, wherein at least one of the functional films is prepared by means of a printing ink composition according to the invention, in particular by printing or coating.
- Suitable electronic devices include, but are not limited to, quantum dot light emitting diodes (QLEDs), quantum dot photovoltaic cells (QPVs), quantum dot luminescent cells (QLEEC), quantum dot field effect transistors (QFETs), quantum dot luminescence field effect transistors, quantum dots. Lasers, quantum dot sensors, etc.
- QLEDs quantum dot light emitting diodes
- QPVs quantum dot photovoltaic cells
- QLEEC quantum dot luminescent cells
- QFETs quantum dot field effect transistors
- quantum dot luminescence field effect transistors quantum dots.
- the electronic device described above is an electroluminescent device, as shown in FIG. 1, comprising a substrate (101), an anode (102), at least one luminescent layer (104), and a cathode. (106).
- the substrate (101) may be opaque or transparent.
- a transparent substrate can be used to make a transparent light-emitting component. See, for example, Bulovic et al. Nature 1996, 380, p29, and Gu et al, Appl. Phys. Lett. 1996, 68, p2606.
- the substrate can be rigid or elastic.
- the substrate can be plastic, metal, semiconductor wafer or glass.
- the substrate has a smooth surface. Substrates without surface defects are a particularly desirable choice.
- the substrate can be selected from a polymer film or plastic having a glass transition temperature Tg of 150 ° C. The above is preferably more than 200 ° C, more preferably more than 250 ° C, and most preferably more than 300 ° C. Examples of suitable substrates are poly(ethylene terephthalate) (PET) and polyethylene glycol (2,6-naphthalene) (PEN).
- PET poly(ethylene terephthalate)
- PEN polyethylene glycol (2,6-naphthalen
- the anode (102) may comprise a conductive metal or metal oxide, or a conductive polymer.
- the anode can easily inject holes into the HIL or HTL or the luminescent layer.
- the absolute value of the difference between the work function of the anode and the HOMO level or the valence band level of the p-type semiconductor material as the HIL or HTL is less than 0.5 eV, preferably less than 0.3 eV, and preferably less than 0.2eV.
- the anode material include, but are not limited to, Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO, aluminum-doped zinc oxide (AZO), and the like.
- anode material can be deposited using any suitable technique, such as a suitable physical vapor deposition process, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), and the like.
- a suitable physical vapor deposition process including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), and the like.
- the anode is patterned.
- Patterned ITO conductive substrates are commercially available and can be used to prepare devices in accordance with the present invention.
- the cathode (106) can comprise a conductive metal or metal oxide.
- the cathode can easily inject electrons into the EIL or ETL or directly into the luminescent layer.
- the absolute value of the difference between the work function of the cathode and the LUMO level or the conduction band level of the n-type semiconductor material as EIL or ETL or HBL is less than 0.5 eV, preferably less than 0.3 eV, preferably It is less than 0.2eV.
- all materials which can be used as cathodes for OLEDs are possible as cathode materials for the devices of the invention.
- cathode material examples include, but are not limited to, Al, Au, Ag, Ca, Ba, Mg, LiF/Al, MgAg alloy, BaF2/Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, ITO, and the like.
- the cathode material can be deposited using any suitable technique, such as a suitable physical vapor deposition.
- the integration method includes RF magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam) and the like.
- the luminescent layer (104) includes at least one luminescent nanomaterial having a thickness between 2 nm and 200 nm.
- the light-emitting layer is prepared by printing the printing ink of the invention, wherein the printing ink comprises a luminescent nano-material as described above, in particular a quantum dot. .
- the light emitting device further comprises a hole injection layer (HIL) or hole transport layer (HTL) (103) containing the organic HTM or inorganic p type as described above. material.
- HIL hole injection layer
- HTL hole transport layer
- the HIL or HTL can be prepared by printing the printing ink of the present invention, wherein the printing ink contains inorganic nanomaterials having hole transporting ability, particularly quantum dots.
- the light emitting device according to the present invention further comprises an electron injection layer (EIL) or electron transport layer (ETL) (105) comprising an organic ETM or inorganic n-type material as described above.
- EIL electron injection layer
- ETL electron transport layer
- the EIL or ETL can be prepared by printing the printing ink of the present invention, wherein the printing ink contains inorganic nanomaterials having electron transporting ability, particularly quantum dots.
- the invention further relates to the use of a light emitting device according to the invention in various applications, including, but not limited to, various display devices, backlights, illumination sources, and the like.
- the two sides of the bottle were stoppered with a rubber stopper.
- the upper part was connected to a condenser tube, and then connected to a double-row tube, heated to 150 ° C, vacuumed for 40 min, and then passed through a nitrogen gas; 12 mL of a syringe was used.
- ODE was added to a three-necked flask.
- 1.92 mL of the solution 1 was quickly injected into a three-necked flask with a syringe for 12 min.
- After 12 min, 4 mL of the solution was added to the three-necked flask with a syringe.
- n-hexane was added to the three-necked flask, and then the liquid in the three-necked flask was transferred to a plurality of 10 mL centrifuge tubes, centrifuged to remove the lower layer precipitate, and repeated three times; acetone was added to the liquid after the post-treatment 1 to precipitate Centrifuge, remove the supernatant, leave a precipitate; then dissolve the precipitate with n-hexane, add acetone to precipitate, centrifuge, remove the supernatant, leave a precipitate, repeat three times; finally dissolve the precipitate with toluene, transfer to glass Stored in the bottle.
- the three-necked flask is placed in a heating flask of 50 mL, vacuum is applied to nitrogen, heated to 150 ° C, vacuum is applied for 30 min, and 7.5 mL is injected. ODE, then reheat to 300 ° C to quickly inject 1 mL of solution 1 for 10 min; 10 min, immediately stop the reaction, the three-necked flask was placed in water to cool.
- the viscosity of the quantum dot ink was tested by a DV-I Prime Brookfield rheometer; the surface tension of the quantum dot ink was tested by a SITA bubble pressure tomometer.
- the quantum dot ink obtained in Example 5 had a viscosity of 6.2 ⁇ 0.1 cPs and a surface tension of 29.1 ⁇ 0.1 dyne/cm.
- the quantum dot ink obtained in Example 6 had a viscosity of 8.3 ⁇ 0.3 cPs and a surface tension of 39.2 ⁇ 0.5 dyne/cm.
- the quantum dot ink obtained in Example 7 had a viscosity of 5.5 ⁇ 0.3 cPs and a surface tension of 32 ⁇ 0.1 dyne/cm.
- the quantum dot ink obtained in Example 8 had a viscosity of 9.8 ⁇ 0.5 cPs and a surface tension of 32.1 ⁇ 0.1 dyne/cm.
- the quantum dot ink obtained in Example 9 had a viscosity of 9.1 ⁇ 0.1 cPs and a surface tension of 39.4 ⁇ 0.3 dyne/cm.
- the quantum dot ink obtained in Example 10 had a viscosity of 9.3 ⁇ 0.3 cPs and a surface tension of 38.1 ⁇ 0.5 dyne/cm.
- the quantum dot ink obtained in Example 11 had a viscosity of 6.7 ⁇ 0.3 cPs and a surface tension of 33.1 ⁇ 0.1 dyne/cm.
- the functional layer in the quantum dot light-emitting diode can be prepared by inkjet printing using the printing ink containing quantum dots based on the substituted aromatic or heteroaromatic solvent system prepared above. Proceed as follows.
- the ink containing the quantum dots is loaded into an ink tank which is mounted on an ink jet printer such as Dimatix Materials Printer DMP-3000 (Fujifilm).
- the waveform, pulse time and voltage of the jetted ink are adjusted to optimize ink jetting and to stabilize the ink jet range.
- the substrate of the QLED is a 0.7 mm thick glass sputtered with an indium tin oxide (ITO) electrode pattern.
- ITO indium tin oxide
- the HIL/HTL material is then inkjet printed into the well and the solvent is removed by drying at elevated temperature in a vacuum to obtain a HIL/HTL film.
- the printing ink containing the luminescent quantum dots is ink-jet printed onto the HIL/HTL film, and the solvent is removed by drying at a high temperature in a vacuum atmosphere to obtain a quantum dot luminescent layer film.
- a printing ink containing quantum dots having electron transporting properties is ink-jet printed onto the light-emitting layer film, and the solvent is removed by drying at a high temperature in a vacuum atmosphere to form an electron transport layer (ETL).
- ETL electron transport layer
- ETL electron transport layer
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Abstract
Description
Claims (18)
- 根据权利要求1所述的印刷油墨组合物,其特征在于,所述的有机溶剂的粘度@25℃,在1cPs到100cPs范围。
- 根据权利要求1所述的印刷油墨组合物,其特征在于,所述的有机溶剂其表面张力@25℃,在19dyne/cm到50dyne/cm范围。
- 根据权利要求1所述的印刷油墨组合物,其特征在于,所述的有机溶剂具有如下通式所示的结构:其中,X是CR1或N;Y选自CR2R3、SiR2R3、NR2、C(=O)、S或O;R1,R2,R3是H,或D,或具有1至20个C原子的直链烷基、烷氧基或硫代烷氧基基团,或者具有3至20个C原子的支链或环状的烷基、烷氧基或硫代烷氧基基团或者是甲硅烷基基团,或具有1至20个C原子的取代的酮基基团,具有2至20个C原子的烷氧基羰基基团,具有7至20个C原子的芳氧基羰基基团,氰基基团(-CN),氨基甲酰基基团(-C(=O)NH2),卤甲酰基基团(-C(=O)-X其中X代表卤素原子),甲酰基基团(-C(=O)-H),异氰基基团,异氰酸酯基团,硫氰酸酯基团或异硫氰酸酯基团,羟基基团,硝基基团,CF3基团,Cl,Br,F,可交联的基团或者具有5至40个环原子的取代或未取代的芳族或杂芳族环系,或具有5至40个环原子的芳氧基或杂芳氧基基团,或这些体系的组合,其中一个或多个基团R1,R2,R3可以彼此和/或与所述基团键合的环形成单环或多环的脂族或芳族环系。
- 根据权利要求1所述的印刷油墨组合物,其特征在于,通式(I)中的R选自具有1至20个C原子的直链烷基、烷氧基或硫代烷氧基基团,或者具有3至20个C原子的支链或环状的烷基、烷氧基或硫代烷氧基基团或者是甲硅烷基基团,或具有1至20个C原子的取代的酮基基团,具有2至20个C原子的烷氧基羰基基团,具有7至20个C原子的芳氧基羰基基团,氰基基团(-CN),氨基甲酰基基团(-C(=O)NH2),卤甲酰基基团(-C(=O)-X其中X代表卤素原子),甲酰基基团(-C(=O)-H),异氰基基团,异氰酸酯基团,硫氰酸酯基团或异硫氰酸酯基团,羟基基团,硝基基团,CF3基团,Cl,Br,F,可交联的基团或者具有5至40个环原子的取代或未取代的芳族或杂芳族环系,或具有5至40个环原子的芳氧基或杂芳氧基基团,或这些体系的组合,其中一个或多个基团R可以彼此和/或与所述基团键合的环形成单环或多环的脂族或芳族环系。
- 根据权利要求1所述的印刷油墨组合物,其特征在于,所述的有机溶剂选自:十二烷基苯、二戊苯、二乙苯、三甲苯、四甲苯、三戊 苯、戊基甲苯、1-甲基萘、二己基苯、二丁基苯、对二异丙基苯、戊苯、四氢萘、环己基苯、氯萘、1-四氢萘酮、3-苯氧基甲苯、1-甲氧基萘、环己基苯、二甲基萘、3-异丙基联苯、对甲基异丙苯、苯甲酸苄酯、二苄醚、苯甲酸苄酯,或它们的任意混合物。
- 根据权利要求1所述的印刷油墨组合物,其特征在于,所述的有机溶剂可以进一步包含至少一种其它溶剂,且通式(I)的有机溶剂占混合溶剂总重量的50%以上。
- 根据权利要求1所述的印刷油墨组合物,其特征在于,其中所述的无机纳米粒子材料是量子点材料,即其粒径具有单分散的尺寸分布,其形状可选自球形、立方体、棒状或支化结构的纳米形貌。
- 根据权利要求1所述的印刷油墨组合物,其特征在于,包含至少一种发光量子点材料,其发光波长位于380nm~2500nm之间。
- 根据权利要求1所述的印刷油墨组合物,其特征在于,其中所述的至少一种的无机纳米材料为元素周期表IV族、II-VI族、II-V族、III-V族、III-VI族、IV-VI族、I-III-VI族、II-IV-VI族、II-IV-V族二元或多元半导体化合物或由这些化合物组成的混合物。
- 根据权利要求1所述的印刷油墨组合物,其特征在于,其中所述的至少一种的无机纳米材料为发光量子点,选自CdSe、CdS、CdTe、ZnO、ZnSe、ZnS、ZnTe、HgS、HgSe、HgTe、CdZnSe及它们的任何组合。
- 根据权利要求1所述的印刷油墨组合物,其特征在于,其中所述的至少一种的无机纳米材料为发光量子点,选自InAs、InP、InN、 GaN、InSb、InAsP、InGaAs、GaAs、GaP、GaSb、AlP、AlN、AlAs、AlSb、CdSeTe、ZnCdSe及它们的任何组合。
- 根据权利要求1所述的印刷油墨组合物,其特征在于,其中所述的至少一种的无机纳米材料为一种钙钛矿纳米粒子材料,特别是发光钙钛矿纳米粒子、或金属纳米粒子材料、金属氧化物纳米粒子材料,或它们的混合物。
- 根据权利要求1所述的印刷油墨组合物,其特征在于,进一步包含至少一种有机功能材料,所述的有机功能材料可选自空穴注入材料(HIM)、空穴传输材料(HTM)、电子传输材料(ETM)、电子注入材料(EIM)、电子阻挡材料(EBM)、空穴阻挡材料(HBM)、发光体(Emitter)、主体材料(Host)。
- 根据权利要求1所述的印刷油墨组合物,其特征在于,无机纳米材料的重量比为0.3%~70%,包含的有机溶剂的重量比为30%~99.7%。
- 一种电子器件,包含有一功能层,其由如权利要求1~16任一项所述的印刷油墨组合物印刷而成,其中组合物中包含的基于取代的芳族或杂芳族的有机溶剂可从溶剂体系中蒸发,以形成无机纳米材料薄膜。
- 根据权利要求17所述的电子器件,其特征在于,所述电子器件可选于量子点发光二极管(QLED)、量子点光伏电池(QPV)、量子点发光电池(QLEEC)、量子点场效应管(QFET)、量子点发光场效应管、量子点激光器、量子点传感器。
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- 2016-07-05 WO PCT/CN2016/088641 patent/WO2017028640A1/zh active Application Filing
- 2016-07-05 US US15/751,103 patent/US20180230321A1/en not_active Abandoned
- 2016-07-05 KR KR1020187002630A patent/KR20180021870A/ko not_active Application Discontinuation
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CN101089058A (zh) * | 2006-06-14 | 2007-12-19 | 三星电机株式会社 | 用于喷墨打印的导电油墨组合物 |
US20090314991A1 (en) * | 2008-01-14 | 2009-12-24 | Samsung Electronics Co., Ltd. | Quantum dot ink composition for inkjet printing and electronic device using the same |
CN101747678A (zh) * | 2008-12-10 | 2010-06-23 | 施乐公司 | 银纳米微粒油墨组合物 |
CN102675965A (zh) * | 2011-03-07 | 2012-09-19 | 施乐公司 | 包含银纳米颗粒的溶剂型油墨 |
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CN116323835A (zh) * | 2020-10-20 | 2023-06-23 | 波音公司 | 邻苯二甲腈基高温电阻性油墨 |
Also Published As
Publication number | Publication date |
---|---|
CN105062193A (zh) | 2015-11-18 |
CN105062193B (zh) | 2020-01-31 |
KR20180021870A (ko) | 2018-03-05 |
US20180230321A1 (en) | 2018-08-16 |
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